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Puerto Rico Cruises Starting In October 2026 and 2027

If you're looking at joining a cruise to Puerto Rico in October 2026 or 2027, we have 26 unique cruise itineraries and 137 departures available, operated by seven of the world's leading cruise lines departing in October.
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26 Cruises (137 Cruise Departures)
13 Day Halloween Transatlantic from Spain with Virgin Voyages
Cruise
 (1)

13 Days (12 Nights) Barcelona to San Juan
Cruise Line: Virgin Voyages
Ship: Scarlet Lady
Departure: 31 October 2027
Visit: Spain, Morocco, Puerto Rico
Limited Time Offer
Inside
$1,143
Oceanview
$1,217
Balcony
$1,331
Suite
$4,875
From
US$1,143
Per Person
View Trip
8 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Icon Of The Seas
Departures: Jun 2026 to Oct 2026
Visit: USA, Virgin Islands, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,577
Oceanview
$1,763
Balcony
$1,880
Suite
$2,720
From
US$1,577
Save 879
Per Person
View Trip
14 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

14 Days (13 Nights) Barcelona to Miami
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 31 October 2026
Visit: Spain, Portugal, Puerto Rico, USA
Inside
$741
Oceanview
$935
Balcony
$1,150
Suite
$6,329
From
US$741
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: MSC Cruises
Ship: MSC World America
Departures: Apr 2026 to Mar 2028
Visit: USA, Dominican Republic, Puerto Rico, Bahamas
Inside
$578
Oceanview
$764
Balcony
$1,004
Suite
$1,444
From
US$578
Per Person
View Trip
15 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

15 Days (14 Nights) Barcelona to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 31 October 2026
Visit: Spain, Portugal, Puerto Rico, USA
Inside
$801
Oceanview
$1,009
Balcony
$1,238
Suite
-
From
US$801
Per Person
View Trip
16 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

16 Days (15 Nights) Palma de Mallorca to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 30 October 2026
Visit: Spain, Portugal, Puerto Rico, USA
Inside
$875
Oceanview
$1,114
Balcony
$1,323
Suite
$2,775
From
US$875
Per Person
View Trip
8 Day Eastern Caribbean with St. Kitts with Princess
Cruise
 (6)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ships: Island Princess, Sky Princess
Departures: Oct 2027 to Feb 2028
Visit: USA, Dominican Republic, Puerto Rico, Saint Kitts and Nevis
Princess Standard
Inside
$534
Oceanview
$694
Balcony
$744
Suite
$1,189
From
US$534
Per Person
View Trip
14 Day West Indies to Spain with Viking Cruises
Cruise
 (5)

14 Days (13 Nights) Barcelona to San Juan
Cruise Line: Viking Cruises
Ship: Viking Sea
Departure: 23 October 2026
Visit: Spain, Portugal, Sint Maarten, Puerto Rico
Viking $999 Air Deal
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$3,299
Suite
$5,999
From
US$3,299
Save 200
Per Person
View Trip
8 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ships: Allure of the Seas, Symphony of the Seas
Departures: Apr 2026 to Oct 2026
Visit: USA, Bahamas, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$861
Oceanview
$931
Balcony
$1,084
Suite
$1,742
From
US$861
Save 493
Per Person
View Trip
10 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

10 Days (9 Nights) New York to New York
Cruise Line: Royal Caribbean
Ship: Oasis of the Seas
Departure: 25 October 2026
Visit: USA, Bahamas, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$1,148
Oceanview
$1,587
Balcony
$1,440
Suite
$3,008
From
US$1,148
Save 668
Per Person
View Trip
8 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Star Of The Seas
Departures: May 2026 to Oct 2027
Visit: USA, Bahamas, Puerto Rico, Saint Martin
Bonus Onboard Credit
Exclusive Savings
Inside
$1,296
Oceanview
$1,451
Balcony
$1,561
Suite
$2,782
From
US$1,296
Save 928
Per Person
View Trip
9 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Adventure of the Seas
Departures: Sep 2026 to Oct 2026
Visit: USA, Virgin Islands, Puerto Rico, Bahamas
Exclusive Savings
Inside
$822
Oceanview
$1,003
Balcony
$1,355
Suite
$2,545
From
US$822
Save 493
Per Person
View Trip
8 Day Eastern Caribbean with Puerto Rico with Princess
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departures: Jul 2026 to Oct 2026
Visit: USA, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$441
Oceanview
$441
Balcony
$611
Suite
$771
From
US$441
Per Person
View Trip
8 Day Southern Caribbean Halloween Cruise with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 31 October 2026
Visit: Puerto Rico, Curacao, Aruba, Martinique, Saint Kitts and Nevis
Limited Time Offer
Inside
$973
Oceanview
$1,183
Balcony
$1,463
Suite
$4,053
From
US$973
Per Person
View Trip
18 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

18 Days (17 Nights) Rome to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 28 October 2026
Visit: Italy, Spain, Portugal, Puerto Rico, USA
Inside
$996
Oceanview
$1,267
Balcony
$1,505
Suite
$6,545
From
US$996
Per Person
View Trip
10 Day Bermuda & Caribbean Cruise: New York, Bermuda & St. Marteen with Azamara Cruises
Cruise
 (3)

10 Days (9 Nights) New York to San Juan
Cruise Line: Azamara Cruises
Ships: Azamara Journey, Azamara Quest
Departures: Oct 2026 to Oct 2027
Visit: USA, Bermuda, Saint Martin, Virgin Islands, Puerto Rico
Azamara Always Included
Inside
$1,529
Oceanview
$2,079
Balcony
$2,587
Suite
$4,497
From
US$1,529
Per Person
View Trip
16 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

16 Days (15 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 30 October 2027
Visit: USA, Bahamas, Mexico, Dominican Republic, Puerto Rico
Inside
$1,359
Oceanview
$1,559
Balcony
$1,919
Suite
$3,397
From
US$1,359
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departures: Sep 2026 to Oct 2026
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Dominica
Exclusive Savings
Inside
$710
Oceanview
$673
Balcony
$1,154
Suite
$1,316
From
US$673
Save 495
Per Person
View Trip
17 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

17 Days (16 Nights) Rome to Miami
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 28 October 2026
Visit: Italy, Spain, Portugal, Puerto Rico, USA
Inside
$929
Oceanview
$1,183
Balcony
$1,408
Suite
$7,648
From
US$929
Per Person
View Trip
15 Day Eastern/Western Caribbean Adventurer with Princess
Cruise

15 Days (14 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departures: Jul 2026 to Oct 2026
Visit: USA, Puerto Rico, Dominican Republic, Turks and Caicos Islands, Bahamas
Princess Standard
Inside
$856
Oceanview
$928
Balcony
$1,376
Suite
-
From
US$856
Per Person
View Trip
9 Day Eastern Caribbean with Puerto Rico with Princess
Cruise
 (1)

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Regal Princess
Departures: Oct 2026 to Feb 2027
Visit: USA, Saint Martin, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$569
Oceanview
-
Balcony
$849
Suite
$1,069
From
US$569
Per Person
View Trip
10 Day Boston To San Juan Cruise with Celebrity Cruises
Cruise

10 Days (9 Nights) Boston to San Juan
Cruise Line: Celebrity Cruises
Ship: Celebrity Summit
Departure: 20 October 2027
Visit: USA, Dominican Republic, Virgin Islands, Antigua and Barbuda, Puerto Rico
Exclusive Savings
Inside
$1,004
Oceanview
$1,054
Balcony
$1,229
Suite
$3,590
From
US$1,004
Save 526
Per Person
View Trip
19 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

19 Days (18 Nights) Genoa to Miami
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 26 October 2026
Visit: Italy, Spain, Portugal, Puerto Rico, USA
Inside
$1,099
Oceanview
$1,359
Balcony
$1,582
Suite
$3,343
From
US$1,099
Per Person
View Trip
9 Day Baltimore To San Juan Cruise with Royal Caribbean
Cruise

9 Days (8 Nights) Baltimore to San Juan
Cruise Line: Royal Caribbean
Ship: Vision of the Seas
Departure: 21 October 2027
Visit: USA, Turks and Caicos Islands, Aruba, Curacao, Puerto Rico
Bonus Onboard Credit
Exclusive Savings
Inside
$646
Oceanview
$727
Balcony
$1,471
Suite
$2,071
From
US$646
Save 375
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ships: Grandeur of the Seas, Rhapsody of the Seas
Departures: May 2027 to Apr 2028
Visit: Puerto Rico, Virgin Islands, Sint Maarten, Saint Lucia, Barbados
Bonus Onboard Credit
Exclusive Savings
Inside
$689
Oceanview
$766
Balcony
$1,248
Suite
$1,473
From
US$689
Save 568
Per Person
View Trip
8 Day Eastern Caribbean With Puerto Rico & Celebration Key with Princess
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Star Princess
Departures: Oct 2027 to Feb 2028
Visit: USA, Bahamas, Dominican Republic, Puerto Rico, Turks and Caicos Islands
Princess Standard
Inside
$739
Oceanview
$899
Balcony
$949
Suite
$1,299
From
US$739
Per Person
View Trip
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